


Day Twenty-Four:Pegging

by TobytheWise



Series: 2018 Kinktober [24]
Category: Supernatural
Genre: Ass Play, Bottom Dean, Multi, Panties, Panty Kink, Pegging, Rimming, Spitroasting, Threesome - F/M/M, Top Castiel
Language: English
Status: Completed
Published: 2018-10-24
Updated: 2018-10-24
Packaged: 2019-08-06 18:48:54
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,057
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16393172
Author URL: https://archiveofourown.org/users/TobytheWise/pseuds/TobytheWise
Summary: “Cas, all our friends are dead.”“Just trust me. It’s someone you used to know who just so happens to be in town.”“I have no idea who you could be talking about, Cas,” Dean murmurs as he shoves a breadstick in his mouth, chewing as aggressively as he can manage right at his angel.“Dean?” comes a voice from above him as a woman walks up to their table. Dean looks up at an absolute blast from the past. He stares at the woman, willing his brain to catch up.“Rhonda,” Cas greets, standing up and pulling her seat out for her. “I’m so glad you could join us tonight.”“The pleasure is all mine.”





	Day Twenty-Four:Pegging

“What do you mean someone’s joining our date?” Dean stares at Cas until the angel explains himself further.

“Just as I said. Someone is joining us tonight.”

“Who? Why?” Dean scrunches up his face before blurting out, “Cas, all our friends are dead.”

“Just trust me. It’s someone you used to know who just so happens to be in town.”

“I have no idea who you could be talking about, Cas,” Dean murmurs as he shoves a breadstick in his mouth, chewing as aggressively as he can manage right at his angel. 

“Dean?” comes a voice from above him as a woman walks up to their table. Dean looks up at an absolute blast from the past. He stares at the woman, willing his brain to catch up. 

“Rhonda,” Cas greets, standing up and pulling her seat out for her. “I’m so glad you could join us tonight.”

“The pleasure is all mine.”

It’s been years since Dean has seen Rhonda but he can tell it’s the same girl from all those years ago. He’d recently retold the tales of Rhonda to Cas, telling him all the things she taught him and how his one regret was not letting Rhonda try the one thing she always begged him for, to let her peg him. He was too insecure to try something like that at that age. Now? Now Dean would pretty much try anything at least once. 

“Wow,” Dean breaths taking all of Rhonda in. Her long blond hair is in a braid that’s pulled across her left shoulder. She’s wearing nice jeans that hug her curves just right and a nice fitted henley under a black leather jacket. She’s just as beautiful as she was when they were teenages. “I can’t believe you’re here. It’s been so fucking long.”

A smile plays across her full lips which are glossed. “It’s been a long time, Dean. Never thought I’d see you again after you skipped town with your dad and brother.”

Cas reaches across the table and squeezes Dean’s hand. “Rhonda knows the just of what we do. She understands you had to leave.”

Rhonda squeezes his thigh under the table. A gasp gets caught in Dean’s throat at the feel of her hands on his body again, regardless of how innocent the act is. “No frowney face, Dean. Tonight’s about having some fun.”

Dean smiles back at Cas before turning to Rhonda. “What sorta fun we talking about?”

~~~

Dean watches as Cas and Rhonda kiss. She’s slightly shorter than Cas so he has to lean down to kiss her. Their tongues mix and she lets out a moan as Cas grabs her ass, thrusting his hard cock against her.

“Fuck,” he whispers to himself, his hand gripping his cock through his jeans. Both sets of blue eyes turn towards him, Rhonda’s a crystal blue which are much lighter than Cas’. 

“Don’t feel left out, baby,” Cas says as he raises a hand to guide him towards them. 

Dean somehow ends up in between them with Cas fucking his mouth with his tongue and Rhonda’s hands explore his chest while kissing the back of his neck. HIs cock throbs painfully where it’s trapped against the zipper of his jeans. 

“I think we’re all wearing far too many clothes,” Rhonda whispers right against his ear causing him to shiver. He nods his head in agreement.

Rhonda steps back, leaving Dean missing the warm contact instantly but Cas makes up for it, running his hands up and down Dean’s body. Cas gently tugs his flannel off before removing his under shirt. 

“Mmm,” Rhonda purs from behind Dean. “Look at you.”

Dean’s face flushes as he spins around to find Rhonda in only her black bra and lacy black panties. Her curvy hips look perfect wrapped up in the black lace. She’s so much more mature and grown into herself since they were teenagers fooling around. 

“Still as gorgeous as I remember, Rhonda.”

Rhonda smiles a devilish grin before walking up and touching his chest. Her hands play with his nipples as her lips reach up to meet his. Dean can hear rustling behind him as Cas begins to strip out of his clothes but he’s too occupied with Rhonda’s talented tongue in his mouth to give it much thought. 

When Rhonda pulls away, Dean’s left panting and aching for more. She gives him yet another grin before pulling her panties completely off and holding them between the two of them. She raises her eyes brow before asking, “just like old times?”

Dean’s face flushes bright red at the reminder of what they used to do together. Behind him, Cas gives a chuckle. He places his hands on Dean’s hips as he looks at Rhonda from over Dean’s shoulder. “That won’t be necessary.”

Rhonda’s breath hitches as Cas opens Dean’s jeans revealing Dean’s red panties. Dean looks shyly at his feet but Rhonda pushes his chin up with one finger. “You look gorgeous in these, and they actually fit you,” she adds with a little giggle. 

Dean lets out a relieved chuckle. He makes his way over to the bed and sits down. “So how do you wanna do this?” he asks, mostly looking to Cas because they both know he’s the one in charge. 

Cas looks over at Rhonda and asks, “would you like to prepare him or would you like me to do it?”

Rhonda bites her lower lips. “Can I rim him?”

Dean lets out a groan at the thought. Yes, he wants that!

“Did he ever let you do that before?” She shakes her head. “I think it’s a great idea. Dean,” Cas says, turning his eyes to Dean. “Get on your hands and knees, ass up in the air for Rhonda.”

Rhonda giggles as Dean scrabbles to listen. “So I don’t have to wonder who’s in charge tonight. I like it. I’m usually the one always calling the shots.”

“He likes to be bossed around,” Cas says as he runs a hand down Dean’s spin. 

“I know,” Rhonda says. Dean can feel the bed dip behind him and she gets into place. His panties are pulled down to the top of his thighs. Rhonda’s fingers gently run up and down his ass until he’s shaking with anticipation. 

Cas comes and sits against the headboard. He spreads his legs, giving Dean the perfect view. Dean lets out a whimper as Cas wraps his hand around his own cock, stroking it right in front of Dean’s face. Dean’s so distracted by the gorgeous sight in front of him that he lets out a surprised yelp as Rhonda’s tongue touches him for the first time. 

“Oh fuck,” Dean yelps, burying his face against Cas’ thigh. “Yes.”

Cas begins to rub through Dean’s hair, grounding him in the most soothing way. His body is lite up with pleasure as Rhonda’s tongue slides over his hole, over and over. She swirls it around before going back to long strokes over it. 

“Such a good boy, Dean,” Cas whispers from above him, continuing his soothing strokes. 

Dean lets out a moan as one of Rhonda’s wet fingers enter him. She continues to lavish his hole with attention from her tongue as her finger gently presses all the way in and then slowly pulls out, opening him up and preparing him. 

Cas tosses the bottle of lube they brought down by Rhonda and suddenly Dean is more full as she pushes two fingers inside his ass. The burn is just right as she opens him up, scissoring her fingers inside him. 

“You almost ready, baby? You want Rhonda to fuck you?” 

“Yes. Yes, please,” Dean whimpers as a third finger plunges into his hole. “Fuck.”

Suddenly, Dean is left empty and wanting as Rhonda pulls her fingers free and takes a step back. Dean whimpers as he looks up at Cas with pleading eyes who huffs before nodding his head, giving Dean the okay. Dean surges forward, wrapping his lips around the head of Cas’ cock. 

Dean sucks Cas’ cock just the way the angel likes, reveling in the groans he pulls from Cas’ throat. He watches as Cas tosses Rhonda a condom and it makes Dean’s ass clench with anticipation. 

“Ready, sweetheart?” Rhonda asks behind him as she rubs the tip of her strap on against his hole, swirling it around, teasing him. 

“Yes,” he grits out. “Please.”

Rhonda pushes forward slowly and Dean’s breath catches in his throat. She moves forward until she’s completely seated inside Dean’s ass. Dean whimpers as he noses against Cas’ balls, breathing in the musky scent there, focusing on that until the burn in his ass is manageable. Once he’s ready, Dean nods up at Cas.

“He’s okay. Go ahead and fuck him, Rhonda.”

Dean begins to lick around each of Cas’ balls as Rhonda begins to move. Her movements are measured, control, slowly building Dean’s arousal. He tries to stay focused on worshipping Cas’ body. Rhonda changes the angle slightly and begins to peg Dean’s prostate. 

“Oh fuck,” he yelps against Cas’ thigh. 

Rhonda chuckles as her hands grip his hips, hard enough to leave bruises later. “There it is. Does it feel good, Dean?”

“Yes. Fuck, yes. Harder, Rhonda. Come on, fuck me.”

Cas sits back slightly until his hole is on display for Dean. Dean licks his lips before sticking his tongue out and running it up and down Cas’ crack. 

“Mmm,” Cas hums as he closes his eyes in pleasure. “Good boy, Dean.”

Dean’s chest fills with pride like it always does at those words. He licks back and forth over Cas’ ass, loving the taste he finds there. He molds his lips around Cas’ hole and sucks just as Rhonda reaches around and begins jerking his cock through his panties. The moan he lets out reverberates around Cas’ hole causing the angel to grip his hair and pull him away. 

“Come, Dean,” Cas growls and Dean can do nothing but obey. His cock erupts in Rhonda’s hand, soiling his panties with his cum.

Dean sighs, laying completely flat against the bed on his belly once he’s finished coming. His limbs are loose from the post orgasmic bliss flowing through his body. 

Cas rolls Dean over until he’s on one side of the bed and Cas can sit on the other. “Come here, sweetheart,” Cas says, motioning for Rhonda to come straddle his lap. Cas quickly suits up his cock before pulling the woman down on his lip.

Rhonda moans as she rubs herself against Cas’ hard cock and Dean can see she’s leaving her slickness all over his condomed cock, already so turned on from pegging Dean. She gets up on her knees while Cas angle’s his cock to her opening. 

“Fuck. Yes,” Rhonda breathes as she sinks all the way down. 

Dean turns on his left side, giving himself the best view possible. They’re both beautiful together like this. Rhonda begins moving, lifting herself slowly before plunging back down. Cas runs his fingers up her sides before cupping her jiggling breasts, toying with her nipples which causes her to cry out and tilt her chest towards his face, silently begging for his mouth on her. He doesn’t disappoint, latching on and sucking on her nipples. 

“Fuck,” Dean sighs, watching them. He runs one hand down Rhonda’s back, including himself. 

“Yes. Touch me, Dean. Please.” Rhonda’s movements speed up, riding Cas’ cock and only worrying about chasing her own pleasure. 

Dean licks his middle finger then moves it to grab her ass. He squeezes her cheek before tapping her asshole with his middle finger. “Oh fuck,” she whimpers as he rubs her asshole and feeling her clench around it. 

“I’m so close,” she groans, throwing her head back in pleasure. Cas moves one of his hands down, rubbing her clit with his thumb. Rhonda cries out as she comes, her hips jerky as she rides it out. 

Rhonda lifts herself from Cas’ lap and flops down beside Dean. She’s panting and sweaty but has a big grin on her face. 

Cas removes his soiled condom, which Dean didn’t even realize he’d come in, and lays on the other side of Rhonda. 

“So,” she whispers. “Round two tomorrow morning before I have to go home?”

Cas just chuckles before replying, “absolutely.”


End file.
